From the art-filled colours of Miami to quirky vintage Palm Springs and always trendy New York, the U.S. has some of the most gorgeous boutique hotels in the world. While recently in Chicago, we had the chance to check-in at The Guesthouse Hotel, and we were impressed by absolutely everything, from the service to epic rooftop views.

While this stay was complimentary, all thoughts and opinions are our own.

The Guesthouse Hotel review

First impressions

The guesthouse hotel Clubroom
Spend some time in the Clubroom (Photo: Ayuma Photography)

Upon arrival, I was greeted by the most friendly, attentive front desk staff, who ensured a smooth and efficient check-in process. The hotel exudes a charming and elegant ambience, with tastefully decorated common areas that immediately set a comfortable tone for the stay.

The lobby feels chic yet collected over time, rather than stuffy or contrived. You’ll notice leather Chesterfield sofas, a crystal chandelier, an eclectic gallery wall of art, local goods from Chicago artisans and makers, and crisp, white walls. The flood of natural light streaming in was just the cherry on top.

Your Chicago oasis

2-bedroom apartment at The Guesthouse Hotel
Our unit was extremely spacious and packed with extras (Photo: Ayuma Photography)

Entering my unit, I was blown away by the spaciousness (1000 sq-ft and 10-ft-high ceilings, to be exact). A unique fact that I learned about The Guesthouse Hotel while I was visiting is that the units were originally built to be condos for full-time residents. This feels completely evident when you see the space.

My husband and I stayed in the two-bedroom, two-bath unit, and it offered more than enough space for us and would have been just as comfortable with another couple. The stand-out feature was the kitchen, which was far from your average extended-stay cook space. It came equipped with a huge granite kitchen island, full-sized appliances, beautiful white kitchen cabinetry, and all the odds and ends you need to prepare a meal properly.

The other major perks we were thrilled about were the closets (including a massive walk-in off the primary bedroom) and the washer and dryer. We were able to return home with suitcases full of clean clothes for the first time, maybe, ever.

In the bedroom, the tranquil decor was a welcome respite from weeks of travel. We had every intention of going out to explore the city that night, but with such a comfortable place to call our own, we decided to order in Chinese and indulge in a hot shower and an early bedtime.

Another highlight was the balcony off of the living room, with our very own grill. Had we stayed another night or two, we definitely would have cracked open a few local beers and given it a go!

The attention to detail was evident at every turn, with all of the toiletries and extras that you’d expect to find in a hotel (like shampoo, conditioner, and coffee). Truly the best of both worlds.

Overall, the expansive and thoughtful space truly made us feel like we were renting our own apartment in the city, and it made my heart soar to live like such a local again in the place I used to call home.

Amenities that pack a punch

Lobby The Guesthouse Hotel
Expect a warm welcome from check-in (Photo: Ayuma Photography)

The hotel facilities were equally impressive, especially for the size of the property. The fitness centre, while small in square footage, was extremely well-maintained and offered state-of-the-art equipment, including a Peloton bike.

The hotel also offers thoughtful conveniences, like on-site parking, and everything you could possibly need if you’re a family traveling with little ones. I had a peek inside their supply closet, and trust me when I say that whether you need a stroller, a bouncer, a travel cot, toys, or any other miscellaneous item, the chances are, they’ll have it for you.

Another perk I so appreciate? The whole property is dog-friendly!

But perhaps the most incredible (and highly unexpected) amenity was the rooftop terrace that provided stunning views of the Chicago skyline. It’s not often that you can get such incredible views of the city in the northern neighborhoods, so this is a true commodity. The area is impeccably decorated with comfortable outdoor couches and lounges, leafy plants, and beautiful string lights, making it a perfect spot for relaxation or enjoying a drink with fellow guests.

While there’s technically no restaurant on the property, you can find a little curated mini market in the lobby to purchase local beers, wines, and snacks, and the staff are happy to rattle off plenty of recommendations that are both within walking distance, as well as further afield.

Neighbourhood charm

The location of The Guesthouse Hotel is absolutely perfect for the traveller who wants a taste of what it’s really like to live in Chicago’s neighbourhoods. Andersonville is quirky and charming, with tons of dynamic eateries and bars (try Hopleaf for high-end pub food and craft brews, or Chicago Magic Lounge for speakeasy vibes).

On Clark Street, you’ll find lots of boutique shops and darling vintage stores just waiting to be discovered, but you’re also only a five-minute Uber ride from the beaches on Lake Michigan, or a 15-minute Uber ride from the more bustling downtown.

Find out more about The Guesthouse Hotel

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